Conventionally, a method of a nucleophilic addition reaction to an aldehyde group of an aldehyde compound or an imino group of an imine compound derived from the aldehyde compound has been studied and, in recent years, this nucleophilic addition reaction has drawn attention as a measure for efficiently and asymmetrically synthesizing an amino acid derivative, a hydroxycarboxylic acid or the like as a raw material or a synthesis intermediate for producing a pharmaceutical preparation, an agricultural chemical, a fragrance, a functional polymer or the like.
Under these circumstances, the present inventors have developed and disclosed a method for synthesizing an N-acylated amino acid derivative by a nucleophilic addition reaction to an N-acylimino ester compound by using a polymer-carrying catalyst (Journal of Combinatorial Chemistry, 2001, Vol. 3, No. 5, 401 to 403) and, further, a method for enantioselectively synthesizing these compounds by using a chiral copper catalyst (Org. Lett. Vol. 4, No. 1, 2002, 143 to 145; J. Am. Chem. Soc. Vol. 125, No. 9, 2003, 2507 to 2515).
However, the nucleophilic addition reaction on which the present inventors have studied is limited to such nucleophilic reactants as a silyl enol ether and an alkyl vinyl ether and, accordingly, a subject to which the nucleophilic addition reaction is applied and such application thereof have inevitably been restricted.
Then, under these circumstances, the present invention has an object of providing a method of an enantioselective nucleophilic addition reaction to a carbonyl group which enables an asymmetric synthesis of an α-hydroxy-γ-keto acid compound, an α-hydroxy-γ-amino acid compound or the like which is useful as a raw material or a synthesis intermediate for producing a pharmaceutical preparation, an agricultural chemical, a fragrance, a functional polymer or the like and, further, as an application thereof, a novel synthesis method of the α-hydroxy-γ-keto acid ester or the like.